Boc-Lys(Z)-OH → 1-[N2-[(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysyl]-L-proline Methyl Ester

HRID 622636Notes

Reaction equation

HRID 622636 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[NH:28]1[CH2:36][CH2:35][CH2:34][C@H:29]1[C:30]([O:32][CH3:33])=[O:31].Cl>C(Cl)Cl>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([N:28]1[CH2:36][CH2:35][CH2:34][C@H:29]1[C:30]([O:32][CH3:33])=[O:31])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

4

Reactant 2

HCID 2724765Boc-Lys(Z)-OHHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 186031681-[N2-[(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysyl]-L-proline Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-Lys(Z)-OH (1 equivalent), Pro-OMe hydrochloride (1 equivalent) and TEA (1 equivalent) were dissolved in dry methylene chloride, and WSCD (1 equivalent) was added under cooling with ice. Thereafter, the mixture was stirred at room temperature for 20 hours, and the reaction mixture was washed successively with IN HCl, water, saturated aqueous sodium bicarbonate, water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under vacuum. The resulting crude product was purified by medium-pressure liquid column chromatography on silica gel to obtain the end compound. Boc-Lys(Z)-Pro-OMe (1 equivalent) thus obtained was dissolved in dry methylene chloride, and an excess of trifluoroacetic acid was added. The mixture was stirred (for about 6 hours), and the solvent was distilled off under vacuum to obtain the end compound (oil).

Workup

  1. additionWSCD (1 equivalent) was added
  2. temperatureunder cooling with ice
  3. washthe reaction mixture was washed successively with IN HCl, water, saturated aqueous sodium bicarbonate, water and saturated brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under vacuum
  6. customThe resulting crude product was purified by medium-pressure liquid column chromatography on silica gel
  7. customto obtain the end compound

Sources & evidence

ORD record
ord-6842f6f933cb4105949b82fbd370e1d0
Source dataset
uspto-grants-1988_09
Patent number
US04772587

Reaction notes

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